Glycol ethers

The name Cellosolve was registered in 1924 as a United States trademark by Carbide & Carbon Chemicals Corporation (a division of Union Carbide Corporation) for "Solvents for Gums, Resins, Cellulose Esters, and the Like". Ethyl Cellosolve, or simply Cellosolve, consists mainly of ethylene glycol monoethyl ether and was introduced as a lower-cost solvent alternative to ethyl lactate. Butyl Cellosolve (ethylene glycol monobutyl ether) was introduced in 1928, and Methyl Cellosolve (ethylene glycol monomethyl ether) in 1929.

Glycol ethers are designated E-series or P-series for those made from ethylene oxide or propylene oxide, respectively. Typically, E-series glycol ethers are found in pharmaceuticals, sunscreens, cosmetics, inks, dyes and water-based paints, while P-series glycol ethers are used in degreasers, cleaners, aerosol paints and adhesives. Both E- and P-series glycol ethers can be used as intermediates that undergo further chemical reactions, producing glycol diethers and glycol ether acetates. P-series glycol ethers are marketed as having lower toxicity than the E-series.

Most glycol ethers are water-soluble, biodegradable and only a few are considered toxic.

In the early 1990s, studies found a higher than expected rates of human reproductive health issues in both males and females, such as elevated risk of miscarriages among women who worked in semiconductor plants as well as male gonadal changes such as testicular atrophy and sperm morphology changes, which was traced back to glycol ethers; in particular: ethylene glycol ethers (diethylene glycol dimethyl ether or ethylene glycol monoethyl ether acetate) used in the photoresist substances that coat semiconductors.

One study suggests that occupational exposure to glycol ethers is related to lowering the motility of the sperm and sperm count, a finding disputed by the chemical industry.

Monoalkyl ethers

• Ethylene glycol monomethyl ether (2-methoxyethanol, CH₃OCH₂CH₂OH)
• Ethylene glycol monoethyl ether (2-ethoxyethanol, CH₃CH₂OCH₂CH₂OH)
• Ethylene glycol monopropyl ether (2-propoxyethanol, CH₃CH₂CH₂OCH₂CH₂OH)
• Ethylene glycol monoisopropyl ether (2-isopropoxyethanol, (CH₃)₂CHOCH₂CH₂OH)
• Ethylene glycol monobutyl ether (2-butoxyethanol, CH₃CH₂CH₂CH₂OCH₂CH₂OH), a widely used solvent in paintings and surface coatings, cleaning products and inks
• Ethylene glycol monophenyl ether (2-phenoxyethanol, C₆H₅OCH₂CH₂OH)
• Ethylene glycol monobenzyl ether (2-benzyloxyethanol, C₆H₅CH₂OCH₂CH₂OH)
• Propylene glycol methyl ether, (1-methoxy-2-propanol, CH₃OCH₂CH(OH)CH₃)
• Diethylene glycol monomethyl ether (2-(2-methoxyethoxy)ethanol, methyl carbitol, CH₃OCH₂CH₂OCH₂CH₂OH)
• Diethylene glycol monoethyl ether (2-(2-ethoxyethoxy)ethanol, carbitol cellosolve, CH₃CH₂OCH₂CH₂OCH₂CH₂OH)
• Diethylene glycol mono-n-butyl ether (2-(2-butoxyethoxy)ethanol, butyl carbitol, CH₃CH₂CH₂CH₂OCH₂CH₂OCH₂CH₂OH)
• Dipropyleneglycol methyl ether
• C12-15 pareth-12 a polyethylene glycol ether used as an emulsifier in cosmetics

Dialkyl ethers

• Ethylene glycol dimethyl ether (dimethoxyethane, monoglyme, CH₃OCH₂CH₂OCH₃), a higher boiling alternative to diethyl ether and THF, also used as a solvent for polysaccharides, a reagent in organometallic chemistry and in some electrolytes of lithium batteries
• Diethylene glycol dimethyl ether (1-Methoxy-2-(2-methoxyethoxy)ethane, diglyme, CH₃OCH₂CH₂OCH₂CH₂OCH₃)
• Triethylene glycol dimethyl ether (2,5,8,11-Tetraoxadodecane, triglyme, CH₃OCH₂CH₂OCH₂CH₂OCH₂CH₂OCH₃)
• Tetraethylene glycol dimethyl ether (2,5,8,11,14-Pentaoxapentadecane, tetraglyme, CH₃OCH₂CH₂OCH₂CH₂OCH₂CH₂OCH₂CH₂OCH₃)
• Ethylene glycol diethyl ether (diethoxyethane, CH₃CH₂OCH₂CH₂OCH₂CH₃)
• Ethylene glycol dibutyl ether (dibutoxyethane, CH₃CH₂CH₂CH₂OCH₂CH₂OCH₂CH₂CH₂CH₃)

Esters

• Ethylene glycol methyl ether acetate (2-methoxyethyl acetate, CH₃OCH₂CH₂OCOCH₃)
• Ethylene glycol monoethyl ether acetate (2-ethoxyethyl acetate, CH₃CH₂OCH₂CH₂OCOCH₃)
• Ethylene glycol monobutyl ether acetate (2-butoxyethyl acetate, CH₃CH₂CH₂CH₂OCH₂CH₂OCOCH₃)
• Propylene glycol methyl ether acetate (1-methoxy-2-propanol acetate)